Vat dyestuffs of the 2-naphthalene-2&#39;-indolindigo series and process of making same



Patented June 6, 1939 .VAT DYESTUFFS OF THE 2-NAPHTHALENE- 2'-INDOLINDIGO SERIES AND PROCESS OF MAKING SAME Werner Zerweck and Walter Brunner, Frankforton-the-Main-Fechenheim, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application May 14, 1937, Serial No. 142,622. In Germany May 19, 1936 4 Claims.

Our present invention relates to vat dyestufis of the .2-naphthalene-2'-indol-indigo series and process of making same more particularly to those of the generalformula:

wherein R stands for a member of the group consisting of alkyl, cycloalkyl, phenyl, alkoxy phenyl and diphenyl, X for a member of the group consisting of hydrogenand halogen and R1 for a member of the group consisting of dihalogenophenyl, alkyl-alkoxy-halogenophenyl,

naphthalene, halogenonaphthalene. The present new vvat dyestufis are obtained by condensing N-alkylor N-aryl-4-hydroxynaphthostyrils with suitable lat-derivatives of the isatin series.

The above specified derivatives of 4-hydroxynaphthostyril may be prepared for instance by heating the mineral acid salts of N-substitution products of 4-amino-naphthostyril or its nuclear substitution products at about 150 to 200 C. in the presence of water advantageously in a closed vessel, whereby the amino group is replaced by the hydroxy group.

The new vat dyestuffs of our present invention dye vegetable fibres mostly bluish grey to blue to green shades of a good fastness particularly to light. The tinctorial properties may be improved in some cases by aftertreatment with a halogenating agent.

In order to further illustrate our invention the following example is given, )the parts ;being by weight and all temperatures in degrees centigrade; but it is, however, to be understood that our invention is not limited to the particular products nor reaction conditions mentioned therein.

Example A mixture of 20 parts of 4-hydroxy-N-methylnaphthostyrile, about 300 parts of chlorobenzene and a solution of 5.7-dichlorisatin-rr-chloride, prepared at 95 to 100 C. from 25 parts of 5.7- dichlorisatin, 25 parts of phosphorus pentachloride and about 500 parts of chlorobenzene, is heated at 80 to 85 C. for some hours. The dyestufi formed is when dry 2. blackish powder, soluble in concentrated sulfuric acid with a blue color, and dyes cotton from a yellowish red vat greenish navy blue shades. It corresponds to the formula:

In the following table there are described some further dyestuffs obtainable according to the present invention;

tgoloriition ofI e so u on o 4 hydroxy naphthostyrfle compound Condensed with a reactive athe dyestufl in Shade of dyeing on derivative of cone Sulfuric cotton acid 4-hydroxy-N-methyl-naphthostyrile.- li-brom-isnflne Blue Gray,

Idem..- 5.7-dlbromo-is fin n Grayish blue.

4-methyl-fi-chloro-y-methoxy-isatine.. Greenish blue. Grayish green. 4.6-dimethyl-fifl-dichloroisatine Blue Navy blue. 2 -nnnhfhi ehnn Reddish brown Green. Dlbl'OIDO-Zl-nanhfhi afinn d Gray, 1-chlor-2.3-naphthisatine Blue Greenish blue. Btorno-l-chlore-2.3-nephthisatine .do Do. 5.6-d1methyl-7-chloro-isatine Grayish black. Navy blue.

-c oro- -nap a me o. Bluel' etur z-lsiga inlo-4-l1ydroxy-N-methyl-naphtho- 5.7-dichloro-isatine Dark blue".-. Gray. quolse n e. Z-glllOl'iJ-i-HYGIOXY-N-IllGthYlflEPhthW 5.7-dichloro-isatine do Bluish gray.

yn e.

4 11 y d r o x y N -(4'-methoxyphenyl)- 5.7-dichloro-isatine Bluish violet. Grayish blue.

nalplhthostynle.

em 4-methyl-E-chloro-7-methoxy-isatine Blue Bluish teen. 4 llaagfiitigszigrlgl -(2-methoxyphenyl)- 4-methyl-5-chloro-7-methoxy-isatine. Dark green Grayisl green. 4-hydroxy-N-diphenyl-naphthostyrile 5.7-dichloro-isatine Bluish bleck-- Grayish green.

Idem 4-methyl-5-chloro-7-methoxy-isatine Bluish green" Greenish blue.

4-hydroxy-N-cyclohexyl-naphthostynle. 5-7-d1chloro-1satine Blue Bluish violet.

Idem 4-methyl-5-chloro-7-methoxy-isatine..- .do..-- Bluish green.

We claim: 1. Vat dyestufis of the 2-naphthalene-2'-indolindigo series of the general formula:

O=CNR wherein R stands for a member of the group consisting of alkylcycloalkyl, phenyl, alkoxy phenyl and diphenyl, X for a member of the group consisting of hydrogen and halogen and R1 for a member of the group consisting of a dihalogenophenyl, alkyl-alkoxy-halogenophenyl, naphthalene, halogenonaphthalene, which dyestuffs dye vegetables fibers mostly bluish gray to blue to green shades of a good fastness particularly to light.

2. A vat dyestufi of the 2-naphthalene-2-indolindigo series of the formula:

which dyestuff is when dry a blackish powder, soluble in concentrated sulfuric acid with a blue color, and dyes cotton from a yellowish red vat greenish navy blue shades. v

3. A vat dyestuff of the 2-naphthalene-2- indolindigo series of the formula:

O=O-NCH3 4) (BOHa which dyestuff is soluble in concentrated sulfuric acid with a greenish blue color and dyes cotton grayish green shades.

4. A vat dyestuif of the 2naphthalene-2'- indolindigo series of the formula:

WERNER ZERWECK. WALTER BRUNNER. 

